tert-Butyl bromoacetate → HCID 117732497, compound

HRID 718631Notes

Reaction equation

HRID 718631 reaction equation
OC(C(F)(F)F)=O.[O:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[N:16]([C:20]([CH:35]4[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]4)=[C:21]([C:23]#[C:24][C:25]4[CH:34]=[CH:33][C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[N:26]=4)[N:22]=3)[N:17]=[CH:18][CH:19]=2)[CH2:10][CH2:9]1.CCN(C(C)C)C(C)C.Br[CH2:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53]>C(Cl)Cl>[O:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[N:16]([C:20]([CH:35]4[CH2:40][CH2:39][N:38]([CH2:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:37][CH2:36]4)=[C:21]([C:23]#[C:24][C:25]4[CH:34]=[CH:33][C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[N:26]=4)[N:22]=3)[N:17]=[CH:18][CH:19]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 81531DiisopropylethylamineHCID 131734173HCID 131734173, compound

Product 1

HCID 117732497HCID 117732497, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 41f (0.15 g, 0.27 mmol) in DCM (3 mL), DIEA (54 mg, 0.42 mmol) was added. The resulting mixture was stirred for 15 min before the addition of tert-butyl 2-bromoacetate (65 mg, 0.33 mmol). The reaction mixture was stirred at rt for 2 h, and concentrated under reduced pressure. The residue obtained was purified by flash column chromatography on silica gel (ethyl acetate:petroleum ether (1:2)) to obtain compound 41g as a yellow solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C32H36N6O3: 553.3 (M+H). found: 553.1.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue obtained
  3. customwas purified by flash column chromatography on silica gel (ethyl acetate:petroleum ether (1:2))

Sources & evidence

ORD record
ord-a3ca784973524718860d10d80984c65b
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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